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    OBI-3424

    DEVELOPMENTS

    PharmaCompass
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    2D Structure
    Also known as: Obi-3424, X6sh5t8h76, Th-3424, 2097713-68-1, 3-(5-((1r)-1-(bis(aziridin-1-yl(phosphoryloxy)ethyl)-2-nitrophenoxy)-n,n-dimethylbenzamide, Unii-x6sh5t8h76
    Molecular Formula
    C21H25N4O6P
    Molecular Weight
    460.4  g/mol
    InChI Key
    NWGZZGNICQFUHV-OAHLLOKOSA-N
    FDA UNII
    X6SH5T8H76
    AKR1C3-activated Prodrug OBI-3424 is a small-molecule nitro-benzene, aldo-keto reductase 1C3 (AKR1C3)-activated prodrug of N,N'-bisethylenephosphoramidate, a DNA bis-alkylating agent, with potential antineoplastic activity. Upon intravenous administration, AKR1C3-activated prodrug OBI-3424 is converted to its active form by AKR1C3, which is upregulated in certain tumor cell types while not expressed in normal healthy cells. The active metabolite selectively binds to and alkylates DNA in AKR1C3-overexpressing tumor cells, resulting in DNA base pair mismatching, interstrand crosslinking and inhibition of DNA repair and synthesis, cell-cycle arrest, and apoptosis. As the expression of AKR1C3 is restricted to tumors, OBI-3424 is selectively converted to its active metabolite in tumor cells only while its conversion in normal, healthy tissue is absent; this allows for an increased cytotoxic effect of the alkylating agent in tumor cells while decreasing its toxicity.
    1 2D Structure

    2D Structure

    2 Identification
    2.1 Computed Descriptors
    2.1.1 IUPAC Name
    3-[5-[(1R)-1-[bis(aziridin-1-yl)phosphoryloxy]ethyl]-2-nitrophenoxy]-N,N-dimethylbenzamide
    2.1.2 InChI
    InChI=1S/C21H25N4O6P/c1-15(31-32(29,23-9-10-23)24-11-12-24)16-7-8-19(25(27)28)20(14-16)30-18-6-4-5-17(13-18)21(26)22(2)3/h4-8,13-15H,9-12H2,1-3H3/t15-/m1/s1
    2.1.3 InChI Key
    NWGZZGNICQFUHV-OAHLLOKOSA-N
    2.1.4 Canonical SMILES
    CC(C1=CC(=C(C=C1)[N+](=O)[O-])OC2=CC=CC(=C2)C(=O)N(C)C)OP(=O)(N3CC3)N4CC4
    2.1.5 Isomeric SMILES
    C[C@H](C1=CC(=C(C=C1)[N+](=O)[O-])OC2=CC=CC(=C2)C(=O)N(C)C)OP(=O)(N3CC3)N4CC4
    2.2 Other Identifiers
    2.2.1 UNII
    X6SH5T8H76
    2.3 Synonyms
    2.3.1 Depositor-Supplied Synonyms

    1. Obi-3424

    2. X6sh5t8h76

    3. Th-3424

    4. 2097713-68-1

    5. 3-(5-((1r)-1-(bis(aziridin-1-yl(phosphoryloxy)ethyl)-2-nitrophenoxy)-n,n-dimethylbenzamide

    6. Unii-x6sh5t8h76

    7. Chembl4297474

    8. Schembl20870529

    9. Obi3424

    10. Obi-3424 [who-dd]

    11. Hy-124573

    12. Cs-0086947

    2.4 Create Date
    2017-05-06
    3 Chemical and Physical Properties
    Molecular Weight 460.4 g/mol
    Molecular Formula C21H25N4O6P
    XLogP32.2
    Hydrogen Bond Donor Count0
    Hydrogen Bond Acceptor Count8
    Rotatable Bond Count8
    Exact Mass460.15117153 g/mol
    Monoisotopic Mass460.15117153 g/mol
    Topological Polar Surface Area108 Ų
    Heavy Atom Count32
    Formal Charge0
    Complexity737
    Isotope Atom Count0
    Defined Atom Stereocenter Count1
    Undefined Atom Stereocenter Count0
    Defined Bond Stereocenter Count0
    Undefined Bond Stereocenter Count0
    Covalently Bonded Unit Count1